A Brønsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.
A Brønsted base activation mode for oxidative, Pd(II)/n class="Chemical">sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.
Authors: Andrew J Hirsh; Bruce F Molino; Jianzhong Zhang; Nadezhda Astakhova; William B Geiss; Bruce J Sargent; Brian D Swenson; Alexander Usyatinsky; Michael J Wyle; Richard C Boucher; Rick T Smith; Andra Zamurs; M Ross Johnson Journal: J Med Chem Date: 2006-07-13 Impact factor: 7.446
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